Organic Chemistry I Lab (CHGN 223)
Fall 2023
** IMPORTANT NOTE **
In the current highly uncertain COVID-19 pandemic landscape,
it is possible that the delivery mode of this course may need to
be changed temporarily and with short notice.
PLEASE READ THIS CAREFULLY BEFORE COMING TO LAB!
LAB COURSE DETAILS
Location
Coolbaugh Hall (CO), Lab 324 - walk past Lab 320 and the two chemical cabinets, turn right
down the hall, and it’s the last door on the right.
Course Material
1) Organic Chemistry I Lab Manual by Cengage Learning
2) CSM Handouts (provided prior to the lab assignment)
Notebook
A lab notebook with carbon copies is required. The carbon copies are turned in to the TA for
grading. The original copy is for your records, as verification that you were in attendance and did
the work. In addition, you retain your notebook to prepare for the next lab.
Instructors
POSITION
NAME
OFFICE
EMAIL
Course Coordinator
Dr. Dylan Domaille
CO 162
ddomaille@mines.edu
Dr. Dylan Domaille
CO 162
ddomaille@mines.edu
Dr. Dan Knauss
CO 158
Dr. Mike McGuirk
CO 160
dknauss@mines.edu
cmmcguirk@mines.edu
Dr. Jim Ranville
CO 256
CO 121
jranvill@mines.edu
yuanyang@mines.edu
Lab Professors
Dr. Yuan Yang
Yooran Im
Jesse Hudspeth
Teaching Assistants
Tristan Huskie
Dina Liacopoulos
yim@mines.edu
Office hours and
jessehudspeth@mines.edu
location will be
tristan_huskie@mines.edu
provided
dliacopoulos@mines.edu
by the TA.
spencer_smith@mines.edu
Spencer Smith
Lab Manager
Ramona Figueroa
CO 311
rfiguero@mines.edu
Lab Schedule
DAY
Tuesday
Wednesday
Thursday
SECTION
TIME
TA
INSTRUCTOR
A
8:00 am
Spencer Smith
Dr. Yang
B
11:00 am
Yooran Im
Dr. Domaille
C
2:00 pm
Spencer Smith
Dr. Knauss
D
11:00 am
Jesse Hudspeth
Dr. Yang
E
2:00 pm
Jesse Hudspeth
Dr. Ranville
F
8:00 am
Tristan Huskie
Dr. Yang
G
11:00 am
Dina Liacopoulos
Dr. Yang
H
2:00 pm
Tristan Huskie
Dr. McGuirk
WEEKLY ACTIVITY
DATE
August 29, 30, 31
EXPERIMENT
Check In:
Introductions, Lab Policies, Drawer and Equipment
Assignments, and Expectations
TECH 700:
Practicing Safety in the Organic Chemistry Laboratory
Safety Contract and Quiz. page 1
September 5, 6, 7
TECH 701:
Measuring the Melting Points of Compounds & Mixtures, page 29
September 12, 13, 14
TECH 703:
Purifying Acetanilide by Recrystallization, page 43
TECH 704:
Separating Cyclohexane and Toluene by Distillation, page 57
September 19, 20, 21
September 26, 27, 28
October 3, 4, 5
October 10, 11, 12
October 16, 17
October 18, 19, 24
October 25, 26, 31
Macroscale Distillation, Part 1. Simple ONLY, page 63
TECH 705:
Separating Acids and Neutral Compounds by Solvent Extraction,
page 81 Microscale Extraction, page 86
SYNT 719:
Br2,
Brominating Alkenes, page 101 Green Chemistry, in situ
Microscale (using trans-Stilbene ONLY), page 108
HANDOUT:
Greener Bromination of Stilbene Greener Chemistry, in situ Br2,
Better Atom Economy
FALL BREAK: No Labs on Tuesday
HANDOUT:
Conformation of Alkylcyclohexanes (Stereochemistry)
ADF Computational Exercise
HANDOUT:
Investigating Nucleophilic Substitution Reactions
ADF Computational Exercise
REAC 714:
November 1, 2, 7
Studying SN1 and SN2 Reactions:
Nucleophilic Substitution at Saturated Carbon, page 115
Factors Affecting the Rates of SN1 Reactions, page 125
November 8, 9, 14
REAC 712:
Dehydrating Cyclohexanol, page 133
Microscale Dehydration Using a Hickman Still Assembly, page 141
November 15, 16, 21
HANDOUT:
Gas Chromatography AND PARTIAL CHECK-OUT
November 22, 23, 24
HOLIDAY:
No Labs on Wednesday and Thursday
HANDOUT:
Spectroscopy - Using FTIR, MS & NMR to Determine the
Identity of an Unknown Compound AND FINAL CHECK-OUT
November 28, 29, 30
LAB NOTEBOOK REQUIREMENTS
All experimental procedures, notes and data are to be kept in a bound notebook. The following
guidelines are to be followed in order to keep an accurate laboratory record. Someone should
be able to duplicate your experimental work and results by reproducing the written
information in your notebook.
1. Number all pages in your laboratory notebook using permanent ink.
2. Reserve a couple of pages in the beginning of the notebook for a table of contents.
3. Make all entries in your lab notebooks in permanent ink (i.e. not water soluble).
4. Write in third person, past tense as an objective observer.
5. Do not remove any pages from your notebook.
6. Draw only one line through entry errors, and write the correct information directly
below.
7. Place a single diagonal line through any blank space in your notebook.
8. Prior to lab: Read all assigned material. Complete the pre-lab assignment and turn it in
to the TA at the beginning of lab. Enter the experimental objective and SDS into your lab
book to be checked by the TA before lab. Points will be deducted if these entries are
incomplete. A mechanism is required only for a chemical synthesis. If the pre-lab
assignment is not complete upon arrival to lab, you will not be allowed to do the
experiment.
9. During lab: Enter your experimental procedures (including alterations, spills, accidents,
restarts, etc.), observations, data, weight of product, % yield of product, melting point
range or boiling point range, product color, etc. in your notebook as you do the
experiment, not before you come to lab or at a later time. Do not tape or paste anything
into the notebook. Any spectra obtained from instrumental analysis should be attached to
your report.
10. Sign and date your notebook at the end of each lab period.
11. OBTAIN YOUR TA’S OR INSTRUCTOR’S SIGNATURE IN YOUR NOTEBOOK AT
THE END OF EACH LAB PERIOD. This provides verification that you actually
attended and completed the lab. If there is no TA or Instructor signature, you will receive
a zero for that lab.
12. Cheating in any form is not tolerated. All laboratory work and notebooks are to be done
on an individual basis. Copying or using another student’s work will result in
a FAILING GRADE for the course and for all students involved.
LAB NOTEBOOK REQUIREMENTS continued
It is important that you know the potential hazards associated with the compounds you are using
and how to handle them safely. The labs are designed to avoid use of toxic or carcinogenic
compounds, but you should be aware of the hazards ahead of time.
Table 1: Example of a Table of Properties
Compound
MW
Amt.
(g/mol) Used
mmol
bp(°C) mp(°C) d
liquids solids
(g/cm3)
SDS
Section 7 Section 8
Section 9
Handling Protection Properties color/state
2137.0
Bromobutane
100
mL
0.92
91.2
-
1.26
VE
GG, GL
Benzaldehyde 106.1
200
mL
1.96
178
-
1.04
VE
GG, GL
Phosgene
98.9
10
mL
0.14
8
-
1.43
FH
GG, GL
Adipic acid
146.1
500
mg
3.4
-
153
1.35
VE
GG, GL
Benzene
FH
GG, GL
Toluene
VE
GG, GL
Ethanol
VE
GG, GL
Nitric Acid
VE
GG, GL
Ethyl ether
VE
GG, GL
Use acronyms in your table for the SDS information. You do not need to write the definitions in
your lab book. Specifically, look for the SDS properties of the chemicals you’ll to use for the
upcoming lab.
Handling: FH = Use in fume hood, VE = Use in ventilated area (on lab bench)
Protection: GG = Goggles, GL = Gloves
LAB GRADING
Pre-lab Report (Assigned Questions).................................. 5 points
Lab Notebook (Recommended Organization)
Objective.................................................................. 2 points
Chemical Properties Table (MSDS)......................... 3 points
Mechanism for a synthesis reaction....................... 5 points
Procedure................................................................. 5 points
Results & Observations......................................... 15 points
Conclusion.............................................................. 10 points
Post-lab Report (Assigned Questions)................................ 5 points
Total
50 points
Tardies, Absences,............................................................... 0 points
Incomplete Reports, No Report Submitted,
No TA Signature in notebook to verify lab completion
GENERAL LAB POLICIES
Lab Attendance
YOU MUST BE ON TIME FOR EACH LAB SESSION. If you come later than the start of the
lab, you will NOT be admitted to the lab, and you will receive a zero grade for that
lab. Continued tardiness will result in a failing grade.
Pre-Lab Assignments
You must have your pre-lab assignment completed and turned in to the TA at the beginning of
your assigned lab period. The completion of the pre-lab assignment is our evidence that you
have read the lab assignment before coming to lab and are prepared to do the experiment. If the
pre-lab assignment has not been completed, you will not be allowed to perform the experiment
and you will receive a zero grade for that lab.
Lab Make Up
No make-up labs are offered. To accommodate absences (excused or not), all student grades
will be calculated after removing the lab report with the lowest score. Multiple excused absences
will be handled on a case-by-case basis by determining the grade on only completed
experiments.
Lab Reports
Lab reports must be turned in at the beginning of the lab period the following week, or when
necessary, on the date requested by the TA. Lab grades will be deducted by 5 points for the first
day it is late and 3 points for each day thereafter. If no report is turned in to the TA by the fifth
late day, a zero grade will be given for that lab.
Lab Dress
All students must wear approved safety GOGGLES (not safety glasses) at ALL times – NO
EXCEPTIONS.
Please note that goggles are not the same as the glasses you wore in General
Chemistry. Contact lenses are strongly discouraged. Gloves are required, but may be limited
and furnished. The following personal protection is required: 1) at least a short-sleeved shirt
that falls below the waist (no exposed skin or undergarments) or a lab coat - sheer or lace shirts
are not permitted; 2) full-length pants (no holes) that cover the ankles, so no skin is
showing. Not permitted are stretchy or tight-fitting pants, such as leggings, jeggings, yoga, or
exercise pants, as well as sleepwear or lounge wear; 3) long socks are strongly encouraged; and
4) shoes that completely cover your ENTIRE foot. This will help to ensure your safety and
avoid unnecessary exposure to hazardous chemicals. Long hair must be tied up in the
back BEFORE YOU ENTER THE LAB, so it does not fall in front of the shoulders and/or
obstruct your vision. Also, any watches, bracelets, necklaces, lanyards, and hats must be kept in
your backpack. Listening devices and cell phones should also remain in your backpack. If you
are dressed inappropriately, the TA, Lab Manager, or Instructor will ask you to leave the lab and
return only when the issue has been resolved.
Lab Cleanliness
An important aspect of working in a lab is to be considerate of others working in that same
space.
Students are required to clean any and all work area(s) and equipment used, including lab
benches, fume hoods, hotplates, balances, melting point apparatus, refractive index apparatus,
gas chromatographs, infrared spectrometers, etc. Points will be deducted from that day’s report
if you fail to clean up after yourself. Please take care of the following items before you leave the
lab.
1. Never leave a chemical spill at your work space, balance, or at any other equipment or
instrumentation in the lab. CLEAN IT UP IMMEDIATELY!! ASK if you are unsure
of the procedure.
2. To clean the bench top, spray DI water (from the wash bottle) over your work area and
wipe with paper towels to remove any chemical residue. Dispose of paper towels in the
solid waste container in the waste hood.
3. Return all of your lab glassware/supplies to your assigned drawer and lock it.
Label All Containers
All containers containing chemicals must be labeled. Use the provided Sharpie marker to write
on the clear part of the glass. Do not write on the white (or frosted) area because it is difficult to
clean. The Sharpie markings are easily removed with methanol sprayed over the liquid
container in the waste hood.
Site for Obtaining FTIR and NMR Literature Spectra
http://sdbs.db.aist.go.jp/sdbs/cgi-bin/cre_index.cgiLinks to an external site.
Important Sites for Obtaining SDS Information
http://www.ilpi.com/msds/Links to an external site.
http://www.ilpi.com/msds/ref/chip.htmlLinks to an external site.
Physical-Chemical Properties1Links to an external site.
Code Letter(s) &
Meaning
Danger
Description
Symbol
E
ExplosiveLinks to an
external site.
Solid, liquid, pasty or gelatinous substances
and preparations which may
react exothermicallyLinks to an external
site. without atmospheric oxygenLinks to
an external site. thereby quickly evolving
gases, and which under defined test
conditions detonate,
quickly deflagrateLinks to an external
site. or upon heating explode when partially
confined.
F+
Extremely FlammableLinks
to an external site.
Liquid substances and preparations having
an extremely low flash pointLinks to an
external site. and a low boiling pointLinks
to an external site. and gaseous substances
and preparations which are flammableLinks
to an external site. in contact with airLinks
to an external site. at
ambient temperatureLinks to an external
site. and pressureLinks to an external site..
F
Highly FlammableLinks to
an external site.
Substances and preparations which may
become hot and finally catch fire in contact
with airLinks to an external site. at
ambient temperatureLinks to an external
site. without any application of energy,
Solid substancesLinks to an external
site. and preparations which may readily
catch fire after brief contact with a source
of ignition and which continue to burn or to
be consumed after removal of the source of
ignition,
Liquid substances and preparations having a
very low flash pointLinks to an external
site., or
Substances and preparations which, in
contact with waterLinks to an external
site. or damp airLinks to an external site.,
evolve extremely flammable gasesLinks to
an external site. in dangerous quantities.
(none)
FlammableLinks to an
external site.
(no
Liquid substances and preparations having a
symbol) low flash point.Links to an external site.
O
OxidizingLinks to an
external site.
Substances and preparations which give rise
to a highly exothermicLinks to an external
site. reaction in contact with other
substances, particularly flammableLinks to
an external site. substances.
Note: Some of the letters/symbols used in these tables are also
used as TSCALinks to an external site., HMISLinks to an
external site. and/or DoD HMIRSLinks to an external
site. codes, all of which have completely different meanings
and applications! See why we dislike code systems?
Health Effects1Links to an external site.
Note: Some symbols appear more than once in the following table. Please study
the first column carefully.
Code Letter(s) & Danger
Meaning
Symbol
Description
C
CorrosiveLinks to
an external site.
Substances and preparations which may, on contact
with living tissues, destroy them.
N
Dangerous For
The Environment
Substances and preparations which, were they to
enter into the environment, would present or might
present an immediate or delayed danger for one or
more components of the environment.
Does not apply to preparations. In certain cases,
some substances do not need to be labelled with
the danger symbol for this category.
T+
Very toxicLinks to
an external site.
Substances and preparations which in very low
quantitiesLinks to an external site. cause death
or acuteLinks to an external site. or chronicLinks
to an external site. damage to health
when inhaledLinks to an external
site., swallowedLinks to an external
site. or absorbed via the skinLinks to an external
site..
T
ToxicLinks to an
external site.
Substances and preparations which in low
quantitiesLinks to an external site. cause death
or acuteLinks to an external site. or chronicLinks
to an external site. damage to health
when inhaledLinks to an external
site., swallowedLinks to an external
site. or absorbed via the skinLinks to an external
site..
Xi
IrritantLinks to an
external site.
Non-corrosiveLinks to an external site. substances
and preparations which, through immediate,
prolonged or repeated contact with the skin or
mucous membrane, may cause inflammationLinks
to an external site..
Xn
HarmfulLinks to
an external site.
Substances and preparations which may cause
death or acuteLinks to an external
site. or chronicLinks to an external site. damage to
health when inhaledLinks to an external
site., swallowedLinks to an external
site. or absorbed via the skinLinks to an external
site..
Substances and preparations which, if they
SensitizingLinks
(i.e. Xn or are inhaledLinks to an external site. or if
to an external site.
they penetrate the skinLinks to an external site.,
Xi)
are capable of eliciting a reaction
Xn
Sensitizing
by inhalationLinks
to an external site.
by hypersensitizationLinks to an external site. such
that on further exposure to the substance or
preparation, characteristic adverse effects are
produced.
Xi
Sensitizing by skin
contactLinks to an
external site.
CarcinogenicLinks
to an external site.
T - Category
1 1Links to an
external site.
T - Category 2
Xn - Category 3
MutagenicLinks to
an external site.
T - Category
1 1Links to an
external site.
T - Category 2
Xn - Category 3
Toxic for
reproductionLinks
to an external site.
T - Category
1 1Links to an
external site.
T - Category 2
Xn - Category 3
Substances and preparations which, if they
are inhaledLinks to an external
(depends
site. or ingestedLinks to an external site. or if
on
they penetrate the skinLinks to an external site.,
category)
may induce cancerLinks to an external site. or
increase its incidence
Substances and preparations which, if they
are inhaledLinks to an external
(depends
site. or ingestedLinks to an external site. or if
on
they penetrate the skinLinks to an external site.,
category)
may induce inheritable genetic defectsLinks to an
external site. or increase their incidence.
Substances and preparations which, if they
are inhaledLinks to an external
site. or ingestedLinks to an external site. or if
(depends they penetrate the skinLinks to an external site.,
on
may produce or increase the incidence of noncategory) inheritable adverse effects in the progenyLinks to
an external site. and/or of male or
female reproductive functions or capacityLinks to
an external site..